Solid-Phase Synthesis of Oligosaccharides and Glycoconjugates by the Glycal Assembly Method: A Five Year Retrospective

Accounts of Chemical Research

Volumn 31, Issue 10, 1998, Pages 685-695

  Seeberger, Peter H ^a,b,c,d   Danishefsky, Samuel J ^{c,e,f,g,h,i,j,k,l,m}  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b UNIVERSITY OF COLORADO   (United States)

^c MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^d MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^e Talmudical Academy   (United States)

^f YESHIVA UNIVERSITY   (United States)

^g HARVARD UNIVERSITY   (United States)

^h Columbia University ^*  (United States)

ⁱ UNIVERSITY OF PITTSBURGH   (United States)

^j YALE UNIVERSITY   (United States)

^k Laboratory for Bioorganic Chemistry   (United States)

^l Amer Assoc Adv of Arts and Sci   (United States)

^m NATIONAL ACADEMY OF SCIENCES   (United States)

more..

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000328143     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar9600648     Document Type: Article

References (74)

1. Glycoconjugates: Composition, Structure, and Function; Allen, H. J.; Kisalius, E. C., Eds.; Marcel Dekker: New York, 1992; Neoglycoconjugates: Preparation and Applications; Lee, Y. C.; Lee, R. T., Eds.; Academic: London, 1994; Kobata, A. Acc. Chem. Res. 1993, 26, 6, 319.
2. Glycoconjugates: Composition, Structure, and Function; Allen, H. J.; Kisalius, E. C., Eds.; Marcel Dekker: New York, 1992; Neoglycoconjugates: Preparation and Applications; Lee, Y. C.; Lee, R. T., Eds.; Academic: London, 1994; Kobata, A. Acc. Chem. Res. 1993, 26, 6, 319.
3. Glycoconjugates: Composition, Structure, and Function; Allen, H. J.; Kisalius, E. C., Eds.; Marcel Dekker: New York, 1992; Neoglycoconjugates: Preparation and Applications; Lee, Y. C.; Lee, R. T., Eds.; Academic: London, 1994; Kobata, A. Acc. Chem. Res. 1993, 26, 6, 319.
4. Varki, A. Glycobiology 1993, 3, 97.
5. Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Science 1990, 250, 1130; Borman, S. Chem. Eng. News 1993, June 28, 27; Lasky, L. A. Science 1992, 258, 964; Miller, D. J.; Macek, M. B.; Schur, B. D. Nature 1992, 357, 589; Schulze, I. T.; Manger, I. D. Glycoconjugate J. 1992, 9, 63; Yaki, T.; Hirabayashi, Y.; Ishikawa, H.; Kon, S.; Tanaka, Y.; Matsumoto, M. J. Biol. Chem. 1986, 261, 3075; Hindsgaul, O.; Norberg, T.; Le Pendu, J.; Lemieux, R. U. Carbohydr. Res. 1988, 174, 211.
6. Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Science 1990, 250, 1130; Borman, S. Chem. Eng. News 1993, June 28, 27; Lasky, L. A. Science 1992, 258, 964; Miller, D. J.; Macek, M. B.; Schur, B. D. Nature 1992, 357, 589; Schulze, I. T.; Manger, I. D. Glycoconjugate J. 1992, 9, 63; Yaki, T.; Hirabayashi, Y.; Ishikawa, H.; Kon, S.; Tanaka, Y.; Matsumoto, M. J. Biol. Chem. 1986, 261, 3075; Hindsgaul, O.; Norberg, T.; Le Pendu, J.; Lemieux, R. U. Carbohydr. Res. 1988, 174, 211.
7. Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Science 1990, 250, 1130; Borman, S. Chem. Eng. News 1993, June 28, 27; Lasky, L. A. Science 1992, 258, 964; Miller, D. J.; Macek, M. B.; Schur, B. D. Nature 1992, 357, 589; Schulze, I. T.; Manger, I. D. Glycoconjugate J. 1992, 9, 63; Yaki, T.; Hirabayashi, Y.; Ishikawa, H.; Kon, S.; Tanaka, Y.; Matsumoto, M. J. Biol. Chem. 1986, 261, 3075; Hindsgaul, O.; Norberg, T.; Le Pendu, J.; Lemieux, R. U. Carbohydr. Res. 1988, 174, 211.
8. Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Science 1990, 250, 1130; Borman, S. Chem. Eng. News 1993, June 28, 27; Lasky, L. A. Science 1992, 258, 964; Miller, D. J.; Macek, M. B.; Schur, B. D. Nature 1992, 357, 589; Schulze, I. T.; Manger, I. D. Glycoconjugate J. 1992, 9, 63; Yaki, T.; Hirabayashi, Y.; Ishikawa, H.; Kon, S.; Tanaka, Y.; Matsumoto, M. J. Biol. Chem. 1986, 261, 3075; Hindsgaul, O.; Norberg, T.; Le Pendu, J.; Lemieux, R. U. Carbohydr. Res. 1988, 174, 211.
9. Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Science 1990, 250, 1130; Borman, S. Chem. Eng. News 1993, June 28, 27; Lasky, L. A. Science 1992, 258, 964; Miller, D. J.; Macek, M. B.; Schur, B. D. Nature 1992, 357, 589; Schulze, I. T.; Manger, I. D. Glycoconjugate J. 1992, 9, 63; Yaki, T.; Hirabayashi, Y.; Ishikawa, H.; Kon, S.; Tanaka, Y.; Matsumoto, M. J. Biol. Chem. 1986, 261, 3075; Hindsgaul, O.; Norberg, T.; Le Pendu, J.; Lemieux, R. U. Carbohydr. Res. 1988, 174, 211.
10. Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Science 1990, 250, 1130; Borman, S. Chem. Eng. News 1993, June 28, 27; Lasky, L. A. Science 1992, 258, 964; Miller, D. J.; Macek, M. B.; Schur, B. D. Nature 1992, 357, 589; Schulze, I. T.; Manger, I. D. Glycoconjugate J. 1992, 9, 63; Yaki, T.; Hirabayashi, Y.; Ishikawa, H.; Kon, S.; Tanaka, Y.; Matsumoto, M. J. Biol. Chem. 1986, 261, 3075; Hindsgaul, O.; Norberg, T.; Le Pendu, J.; Lemieux, R. U. Carbohydr. Res. 1988, 174, 211.
11. Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Science 1990, 250, 1130; Borman, S. Chem. Eng. News 1993, June 28, 27; Lasky, L. A. Science 1992, 258, 964; Miller, D. J.; Macek, M. B.; Schur, B. D. Nature 1992, 357, 589; Schulze, I. T.; Manger, I. D. Glycoconjugate J. 1992, 9, 63; Yaki, T.; Hirabayashi, Y.; Ishikawa, H.; Kon, S.; Tanaka, Y.; Matsumoto, M. J. Biol. Chem. 1986, 261, 3075; Hindsgaul, O.; Norberg, T.; Le Pendu, J.; Lemieux, R. U. Carbohydr. Res. 1988, 174, 211.
12. Levy, D. E.; Tang, P. C.; Musser, J. H. In Ann. Rep. Med. Chem.; W. K. Hagmann, Ed.; Academic: San Diego, 1994; Vol. 29; p 215.
13. Opdenakker, G.; Rudd, P. M.; Ponting, C. P.; Dwek, R. A. FASEB J. 1993, 7, 1330.
14. Merrifield, B. J. Am. Chem. Soc. 1963, 85, 2149. For a review see: Atherton, E.; Sheppard, R. C. Solid-phase peptide synthesis: A practical approach; IRL Press at Oxford University Press: Oxford, England, 1989; p 203.
15. Merrifield, B. J. Am. Chem. Soc. 1963, 85, 2149. For a review see: Atherton, E.; Sheppard, R. C. Solid-phase peptide synthesis: A practical approach; IRL Press at Oxford University Press: Oxford, England, 1989; p 203.
16. Atherton, E.; Sheppard, R. C. Solid-phase peptide synthesis: A practical approach; IRL Press at Oxford University Press: Oxford, England, 1989, p 203.
17. Caruthers, M. H. Science 1985, 230, 281.
18. For a pioneering effort see: Frechet, J. M. J.; Schuerch, C. Carbohydr. Res. 1972, 22, 399. For a review see: Boons, G.-J. Tetrahedron 1996, 52, 1095. More recent syntheses: Yan, L.; Taylor, C. M.; Goodnow, R.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6953; Nicolaou, K. C.; Winssinger, N.; Pastor, J.; De Roose, F. J. Am. Chem. Soc. 1997, 119, 449; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1997, 119, 5562; Rademann, J.; Schmidt, R. R. J. Org. Chem. 1997, 62, 3650.
19. For a pioneering effort see: Frechet, J. M. J.; Schuerch, C. Carbohydr. Res. 1972, 22, 399. For a review see: Boons, G.-J. Tetrahedron 1996, 52, 1095. More recent syntheses: Yan, L.; Taylor, C. M.; Goodnow, R.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6953; Nicolaou, K. C.; Winssinger, N.; Pastor, J.; De Roose, F. J. Am. Chem. Soc. 1997, 119, 449; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1997, 119, 5562; Rademann, J.; Schmidt, R. R. J. Org. Chem. 1997, 62, 3650.
20. For a pioneering effort see: Frechet, J. M. J.; Schuerch, C. Carbohydr. Res. 1972, 22, 399. For a review see: Boons, G.-J. Tetrahedron 1996, 52, 1095. More recent syntheses: Yan, L.; Taylor, C. M.; Goodnow, R.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6953; Nicolaou, K. C.; Winssinger, N.; Pastor, J.; De Roose, F. J. Am. Chem. Soc. 1997, 119, 449; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1997, 119, 5562; Rademann, J.; Schmidt, R. R. J. Org. Chem. 1997, 62, 3650.
21. For a pioneering effort see: Frechet, J. M. J.; Schuerch, C. Carbohydr. Res. 1972, 22, 399. For a review see: Boons, G.-J. Tetrahedron 1996, 52, 1095. More recent syntheses: Yan, L.; Taylor, C. M.; Goodnow, R.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6953; Nicolaou, K. C.; Winssinger, N.; Pastor, J.; De Roose, F. J. Am. Chem. Soc. 1997, 119, 449; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1997, 119, 5562; Rademann, J.; Schmidt, R. R. J. Org. Chem. 1997, 62, 3650.
22. For a pioneering effort see: Frechet, J. M. J.; Schuerch, C. Carbohydr. Res. 1972, 22, 399. For a review see: Boons, G.-J. Tetrahedron 1996, 52, 1095. More recent syntheses: Yan, L.; Taylor, C. M.; Goodnow, R.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6953; Nicolaou, K. C.; Winssinger, N.; Pastor, J.; De Roose, F. J. Am. Chem. Soc. 1997, 119, 449; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1997, 119, 5562; Rademann, J.; Schmidt, R. R. J. Org. Chem. 1997, 62, 3650.
23. For a pioneering effort see: Frechet, J. M. J.; Schuerch, C. Carbohydr. Res. 1972, 22, 399. For a review see: Boons, G.-J. Tetrahedron 1996, 52, 1095. More recent syntheses: Yan, L.; Taylor, C. M.; Goodnow, R.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6953; Nicolaou, K. C.; Winssinger, N.; Pastor, J.; De Roose, F. J. Am. Chem. Soc. 1997, 119, 449; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1997, 119, 5562; Rademann, J.; Schmidt, R. R. J. Org. Chem. 1997, 62, 3650.
24. (a) Kunz, H.; von dem Bruch, K. Methods Enzymol. 1994, 247, 3.
25. (b) Meldal, M.; St. Hilaire, P. M. Curr. Opin. Cell Biol. 1997, 1, 552.
26. (c) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823.
27. (d) Wong, C.-H. Pure Appl. Chem. 1995, 67, 1609.
28. (e) Meldal, M.; Bock, K. Glycoconjugate 1994, 11, 59.
29. (f) Kappes, T.; Waldmann, H. Top. Curr. Chem. 1997, 186, 65.
30. (g) Danishefsky, S. J.; Roberge, J. Y. In Glycopeptides and Related Compounds: Synthesis, Analysis and Applications; D. G. Large; C. D. Warren, Eds.; Marcell Dekker: New York, 1997; p 245 and references therein.
31. Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661.
32. Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656.
33. Chan, T.-H.; Huang, W.-Q. J. Chem. Soc. Chem. Commun. 1985, 909.
34. Danishefsky, S. J.; McClure, K. F.; Randolph, J. T.; Ruggeri, R. B. Science 1993, 260, 1307.
35. Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847.
36. Randolph, J. T.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 8473.
37. Seeberger, P. H.; Beebe, X.; Sukenick, G.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 491.
38. Race, R. R.; Sanger, R. Blood Groups in Man, 6th ed.; Blackwell: Oxford, 1975.
39. (a) Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Science 1990, 250, 1130.
40. (b) Hirabayashi, Y.; Hyogo, A.; Nakao, T.; Tsuchiya, K.; Suzuki, Y.; Matsumoto, M.; Kon, K.; Ando, S. J. Biol. Chem. 1990, 265, 8144.
41. (c) Spohr, U.; Lemieux, R. U. J. Biol. Chem. 1988, 174, 211.
42. (a) Polley, M. J.; Phillips, M. L.; Wagner, E.; Nudelman, E.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 6224.
43. (b) Hindsgaul, O.; Norberg, T.; Le Pendu, J.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109.
44. For a review see: Lloyd, K. O. Am. J. Clin. Path. 1987, 87, 129.
45. Lloyd, K. O. Cancer Biol. 1991, 2, 421.
46. For some recent syntheses of H-type determinants see: (a) Petrakova, E.; Spohr, U.; Lemieux, R. U. Can. J. Chem. 1992, 70, 233. (b) Zemlyanukhina, T. V.; Bovin, N. V. Bioorg. Khim. 1990, 16, 1096.
47. For some recent syntheses of H-type determinants see: (a) Petrakova, E.; Spohr, U.; Lemieux, R. U. Can. J. Chem. 1992, 70, 233. (b) Zemlyanukhina, T. V.; Bovin, N. V. Bioorg. Khim. 1990, 16, 1096.
48. Nicoloau, K. C.; Hummel, C. W.; Iwabuchi, Y. J. Am. Chem. Soc. 1992, 114, 3126.
49. Boren, T.; Falk, P.; Roth, K. A.; Larson, G.; Normark, S. Science 1993, 262, 1892.
50. Alper, J. Science 1993, 260, 159.
51. (a) Graham, D. Y.; Lew, G. M.; Klein, P. D.; Evans, D. G.; Evans, D. J.; Saeed, Z. A.; Malaty, H. M. Ann. Intern. Med. 1992, 116, 705.
52. (b) Hentschel, E.; Brandstatter, G.; Dragosics, B.; Hirschl, A. M.; Nemeg, H.; Schutze, K.; Taufer, M.; Wurzer, H. N. Eng. J. Med. 1993, 328, 308.
53. Sharon, N. In The Lectins: Properties, Functions and Applicationsin Biology and Medicine; Liener, I. E., Sharon, N., Goldstein, I. J., Eds.; Academic: New York, 1986, pp 494-525.
54. Bernstein, M. A.; Hall, L. D. Carbohydr. Res. 1980, 78, C1.
55. Randolph, J. T.; Danishefsky, S. J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1470.
56. Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112, 5811; Hamada, T.; Nishida, A.; Yonemitsu, O. J. Am. Chem. Soc. 1986, 108, 140.
57. Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112, 5811; Hamada, T.; Nishida, A.; Yonemitsu, O. J. Am. Chem. Soc. 1986, 108, 140.
58. Zheng, C.; Seeberger, P. H.; Danishefsky, S. J. Angew. Chem. Int. Ed. Engl. 1998, 37, 786.
59. For the activation of thiodonors see: Lönn, H. Carbohydr. Res. 1985, 135, 105; Lönn, H. Carbohydr. Res. 1985, 139, 115; Lönn, H. J. Carbohydr. Chem. 1987, 6, 301; Fügedi, P. Garegg, P. J. Carbohydr. Res. 1986, 149, C6.
60. For the activation of thiodonors see: Lönn, H. Carbohydr. Res. 1985, 135, 105; Lönn, H. Carbohydr. Res. 1985, 139, 115; Lönn, H. J. Carbohydr. Chem. 1987, 6, 301; Fügedi, P. Garegg, P. J. Carbohydr. Res. 1986, 149, C6.
61. For the activation of thiodonors see: Lönn, H. Carbohydr. Res. 1985, 135, 105; Lönn, H. Carbohydr. Res. 1985, 139, 115; Lönn, H. J. Carbohydr. Chem. 1987, 6, 301; Fügedi, P. Garegg, P. J. Carbohydr. Res. 1986, 149, C6.
62. For the activation of thiodonors see: Lönn, H. Carbohydr. Res. 1985, 135, 105; Lönn, H. Carbohydr. Res. 1985, 139, 115; Lönn, H. J. Carbohydr. Chem. 1987, 6, 301; Fügedi, P. Garegg, P. J. Carbohydr. Res. 1986, 149, C6.
63. See ref 32. The method has recently been applied to the solid-state synthesis of the breast tumor antigen (globo H) system (Zheng, C. unpublished results).
64. Zheng, C.; Seeberger, P. H.; Danishefsky, S. J. J. Org. Chem. 1998, 63, 3, 1126.
65. Seeberger, P. H.; Eckhardt, M.; Gutteridge, C. E.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10064.
66. Kunz, H.; Harreus, A. Liebigs Ann. Chem. 1982, 41; Kunz, H.; Harreus, A. Liebigs Ann. Chem. 1986, 717.
67. Kunz, H.; Harreus, A. Liebigs Ann. Chem. 1982, 41; Kunz, H.; Harreus, A. Liebigs Ann. Chem. 1986, 717.
68. Kunz, H. Angew. Chem., Int. Ed. Engl. 1987, 26, 294.
69. Meldal, M. Curr. Opin. Struct. Biol. 1994, 4, 710.
70. For recent selected examples see: (a) Cohen-Anisfeld, S. T.; Landsbury, P. T. J. Am. Chem. Soc. 1993, 115, 10531. (b) Vetter, D.; Tumelty, D.; Singh, S. K.; Gallop, M. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 60. (c) Sprenghard, U.; Kretzschmar, G.; Bartnik, E.; Hüls, C.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 60.
71. For recent selected examples see: (a) Cohen-Anisfeld, S. T.; Landsbury, P. T. J. Am. Chem. Soc. 1993, 115, 10531. (b) Vetter, D.; Tumelty, D.; Singh, S. K.; Gallop, M. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 60. (c) Sprenghard, U.; Kretzschmar, G.; Bartnik, E.; Hüls, C.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 60.
72. For recent selected examples see: (a) Cohen-Anisfeld, S. T.; Landsbury, P. T. J. Am. Chem. Soc. 1993, 115, 10531. (b) Vetter, D.; Tumelty, D.; Singh, S. K.; Gallop, M. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 60. (c) Sprenghard, U.; Kretzschmar, G.; Bartnik, E.; Hüls, C.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 60.
73. Roberge, J. Y.; Beebe, X.; Danishefsky, S. J. Science 1995, 269, 202.
74. Lloyd-Williams, P.; Albericio, F.; Giralt, E. Tetrahedron 1993, 49, 1106.